# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fwj2
_database_code_depnum_ccdc_archive 'CCDC 1505900'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Cl2 F2 N O'
_chemical_formula_weight         356.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1569(11)
_cell_length_b                   7.4746(7)
_cell_length_c                   21.679(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.836(10)
_cell_angle_gamma                90.00
_cell_volume                     1634.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1420
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8434
_exptl_absorpt_correction_T_max  0.8987
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16812
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3030
_reflns_number_gt                2317
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0822P)²+2.8985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2062
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.48901(14) 0.20317(17) 0.67777(7) 0.0807(4) Uani 1 1 d . . .
Cl2 Cl 0.71856(12) 0.82390(17) 0.62475(7) 0.0799(5) Uani 1 1 d . . .
F1 F 0.1349(5) 0.2526(6) 0.5118(2) 0.1521(19) Uani 1 1 d . . .
F2 F 0.1066(6) 0.4249(6) 0.5845(3) 0.163(2) Uani 1 1 d . . .
O1 O 0.4416(3) 0.5738(4) 0.57790(12) 0.0565(7) Uani 1 1 d . . .
N1 N 0.4286(3) 0.6787(5) 0.67883(15) 0.0550(9) Uani 1 1 d . . .
C1 C 0.4843(4) 0.5945(5) 0.63827(17) 0.0440(8) Uani 1 1 d . . .
C2 C 0.3244(4) 0.6701(6) 0.54811(18) 0.0537(10) Uani 1 1 d . . .
C3 C 0.2527(4) 0.7641(5) 0.59666(18) 0.0481(9) Uani 1 1 d . . .
C4 C 0.1377(5) 0.8584(7) 0.5796(2) 0.0682(12) Uani 1 1 d . . .
H4 H 0.1012 0.8599 0.5382 0.082 Uiso 1 1 calc R . .
C5 C 0.0754(5) 0.9514(7) 0.6235(3) 0.0727(13) Uani 1 1 d . . .
H5 H -0.0018 1.0156 0.6114 0.087 Uiso 1 1 calc R . .
C6 C 0.1273(5) 0.9484(7) 0.6842(2) 0.0707(13) Uani 1 1 d . . .
H6 H 0.0845 1.0087 0.7136 0.085 Uiso 1 1 calc R . .
C7 C 0.2428(5) 0.8569(7) 0.7025(2) 0.0643(12) Uani 1 1 d . . .
H7 H 0.2784 0.8563 0.7440 0.077 Uiso 1 1 calc R . .
C8 C 0.3065(4) 0.7644(5) 0.65830(18) 0.0475(9) Uani 1 1 d . . .
C9 C 0.3757(5) 0.8038(7) 0.5034(2) 0.0781(14) Uani 1 1 d . . .
H9A H 0.4277 0.8937 0.5267 0.117 Uiso 1 1 calc R . .
H9B H 0.3020 0.8593 0.4788 0.117 Uiso 1 1 calc R . .
H9C H 0.4295 0.7425 0.4767 0.117 Uiso 1 1 calc R . .
C10 C 0.2427(5) 0.5271(7) 0.5123(2) 0.0680(13) Uani 1 1 d . . .
H10A H 0.2939 0.4786 0.4812 0.082 Uiso 1 1 calc R . .
H10B H 0.1643 0.5828 0.4906 0.082 Uiso 1 1 calc R . .
C11 C 0.1995(5) 0.3750(8) 0.5502(3) 0.0822(15) Uani 1 1 d . . .
H11 H 0.2752 0.3212 0.5758 0.099 Uiso 1 1 calc R . .
C12 C 0.6159(4) 0.5090(5) 0.65478(16) 0.0464(9) Uani 1 1 d . . .
C13 C 0.6300(4) 0.3320(6) 0.67512(18) 0.0559(10) Uani 1 1 d . . .
C14 C 0.7540(5) 0.2588(7) 0.6929(2) 0.0696(13) Uani 1 1 d . . .
H14 H 0.7618 0.1415 0.7071 0.083 Uiso 1 1 calc R . .
C15 C 0.8657(5) 0.3614(8) 0.6893(2) 0.0755(14) Uani 1 1 d . . .
H15 H 0.9489 0.3128 0.7017 0.091 Uiso 1 1 calc R . .
C16 C 0.8561(4) 0.5323(7) 0.6679(2) 0.0676(12) Uani 1 1 d . . .
H16 H 0.9320 0.5993 0.6645 0.081 Uiso 1 1 calc R . .
C17 C 0.7324(4) 0.6047(6) 0.65128(19) 0.0554(10) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.732(5) . ?
Cl2 C17 1.736(5) . ?
F1 C11 1.353(6) . ?
F2 C11 1.322(7) . ?
O1 C1 1.338(4) . ?
O1 C2 1.472(5) . ?
N1 C1 1.268(5) . ?
N1 C8 1.420(5) . ?
C1 C12 1.487(5) . ?
C2 C10 1.511(6) . ?
C2 C3 1.521(5) . ?
C2 C9 1.525(6) . ?
C3 C8 1.382(5) . ?
C3 C4 1.377(6) . ?
C4 C5 1.391(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.400(5) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.498(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C12 C17 1.393(6) . ?
C12 C13 1.396(6) . ?
C13 C14 1.385(6) . ?
C14 C15 1.379(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(6) . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 121.6(3) . . ?
C1 N1 C8 116.9(3) . . ?
N1 C1 O1 128.0(3) . . ?
N1 C1 C12 120.6(3) . . ?
O1 C1 C12 111.3(3) . . ?
O1 C2 C10 104.2(4) . . ?
O1 C2 C3 110.5(3) . . ?
C10 C2 C3 113.8(4) . . ?
O1 C2 C9 106.3(3) . . ?
C10 C2 C9 110.2(4) . . ?
C3 C2 C9 111.4(4) . . ?
C8 C3 C4 118.9(4) . . ?
C8 C3 C2 120.2(3) . . ?
C4 C3 C2 120.8(4) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 120.0(4) . . ?
C3 C8 N1 122.2(3) . . ?
C7 C8 N1 117.8(4) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C11 115.8(4) . . ?
C2 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
C2 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
F2 C11 F1 102.2(5) . . ?
F2 C11 C10 111.7(5) . . ?
F1 C11 C10 109.1(5) . . ?
F2 C11 H11 111.2 . . ?
F1 C11 H11 111.2 . . ?
C10 C11 H11 111.2 . . ?
C17 C12 C13 116.6(4) . . ?
C17 C12 C1 120.8(4) . . ?
C13 C12 C1 122.6(4) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 Cl1 119.9(4) . . ?
C12 C13 Cl1 118.9(3) . . ?
C15 C14 C13 119.4(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C12 122.6(4) . . ?
C16 C17 Cl2 119.6(4) . . ?
C12 C17 Cl2 117.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 -0.9(6) . . . . ?
C8 N1 C1 C12 176.7(3) . . . . ?
C2 O1 C1 N1 7.6(6) . . . . ?
C2 O1 C1 C12 -170.2(3) . . . . ?
C1 O1 C2 C10 -131.8(4) . . . . ?
C1 O1 C2 C3 -9.2(5) . . . . ?
C1 O1 C2 C9 111.8(4) . . . . ?
O1 C2 C3 C8 5.7(5) . . . . ?
C10 C2 C3 C8 122.5(4) . . . . ?
C9 C2 C3 C8 -112.2(4) . . . . ?
O1 C2 C3 C4 -178.0(4) . . . . ?
C10 C2 C3 C4 -61.2(6) . . . . ?
C9 C2 C3 C4 64.1(5) . . . . ?
C8 C3 C4 C5 -0.6(7) . . . . ?
C2 C3 C4 C5 -177.0(4) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 C7 1.3(8) . . . . ?
C5 C6 C7 C8 -0.7(8) . . . . ?
C4 C3 C8 C7 1.2(6) . . . . ?
C2 C3 C8 C7 177.6(4) . . . . ?
C4 C3 C8 N1 -176.5(4) . . . . ?
C2 C3 C8 N1 -0.1(6) . . . . ?
C6 C7 C8 C3 -0.6(7) . . . . ?
C6 C7 C8 N1 177.2(4) . . . . ?
C1 N1 C8 C3 -2.9(6) . . . . ?
C1 N1 C8 C7 179.5(4) . . . . ?
O1 C2 C10 C11 59.5(5) . . . . ?
C3 C2 C10 C11 -61.0(5) . . . . ?
C9 C2 C10 C11 173.1(4) . . . . ?
C2 C10 C11 F2 71.6(6) . . . . ?
C2 C10 C11 F1 -176.1(5) . . . . ?
N1 C1 C12 C17 -88.0(5) . . . . ?
O1 C1 C12 C17 89.9(4) . . . . ?
N1 C1 C12 C13 91.1(5) . . . . ?
O1 C1 C12 C13 -90.9(4) . . . . ?
C17 C12 C13 C14 2.2(6) . . . . ?
C1 C12 C13 C14 -177.0(4) . . . . ?
C17 C12 C13 Cl1 -177.6(3) . . . . ?
C1 C12 C13 Cl1 3.2(5) . . . . ?
C12 C13 C14 C15 -1.3(7) . . . . ?
Cl1 C13 C14 C15 178.6(4) . . . . ?
C13 C14 C15 C16 -0.8(7) . . . . ?
C14 C15 C16 C17 1.8(7) . . . . ?
C15 C16 C17 C12 -0.8(7) . . . . ?
C15 C16 C17 Cl2 179.2(4) . . . . ?
C13 C12 C17 C16 -1.2(6) . . . . ?
C1 C12 C17 C16 178.0(4) . . . . ?
C13 C12 C17 Cl2 178.8(3) . . . . ?
C1 C12 C17 Cl2 -2.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.064
